Methyl 3-bromo-5-methoxybenzoate → (3-Bromo-5-methoxyphenyl)methanol

HRID 1453644Notes

Reaction equation

HRID 1453644 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 15618226Methyl 3-bromo-5-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10608788(3-Bromo-5-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

13.5 Grams (55 mmole)) Methyl 3-bromo-5-methoxybenzoate was dissolved in ether and cooled in an ice bath. 33 ml of 1M lithium aluminum hydride was added dropwise. The reaction mix was then quenched cautiously by addition of sodium sulfate decahydrate, then water, and solid residue was removed by filtration. The ether was separated and evaporated under reduced pressure to give 11 gms of 3-bromo-5-methoxy benzyl alcohol as a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. additionThe reaction mix
  3. customwas then quenched cautiously by addition of sodium sulfate decahydrate
  4. customwater, and solid residue was removed by filtration
  5. customThe ether was separated
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1ab5a9eca0004a9a8b37abf942fb1414
Source dataset
uspto-grants-2009_01
Patent number
US07476675B2

Reaction notes

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